The Pharisees must be getting desperate. This
Jesus has come into the Temple in Jerusalem at Passover, its busiest time of the
year, and systematically humiliated and discredited them. First he makes a big
show of overturning the tables of the merchants and moneychangers, accusing them
of defiling God’s holy place, then he begins healing and teaching the people.
When the Pharisees challenge his authority to do all this, he responds in such a
way as to not only claim holy authority for himself, but to also diminish the
authority of the chief priests and Pharisees. This Jesus then goes on to tell a
series of parables that serves to demonstrate how the chief priests and
Pharisees are not working according to the will of God, and even suggesting that
God himself will abandon them in favor of others. They have to do something
drastic to stop this now!

So they gather up some Herodians and confront
him. Now, you’ve got to understand that Jewish religious leaders and Herodians
didn’t usually buddy around together. Herodians were those who represented the
interests of Roman rule in their colonies, which is what Israel was at this
point. Pharisees barely tolerated Herodians, yet they enlisted their help to
confront Jesus. They wanted to trap him with his own words. So they butter him
up with flattery, and then ask him a no-win question: Is it lawful to pay taxes
to the emperor or not?

It’s the perfect trap; if he says ‘yes,’ then
he can be accused of being in collusion with Rome, justifying Roman occupation
and oppression of the Jews. This would destroy his credibility with the people
and solve the Pharisees’ problems. But if he answers ‘no,’ especially in front
of the Herodians, then he can be accused of revolutionary sentiment against
Rome, and addressing those charges would distract him from all this preaching
and teaching he’s been doing. It might even get him arrested and executed
as a criminal.